Tips for Cold-Emailing Intimidatingly Powerful People

CEOs are thirsty for insight from the front lines. And yet those of us on those front lines – whether we are customers or employees – are often hesitant to reach out to senior leaders who are only an email away.

I saw this the other day in a friend who works for Salesforce. My friend is a mid-level manager, and he’s very observant and bright. He has a ton of insight and perspective about Salesforce that Marc Benioff, the founder and CEO of Salesforce, would be better off knowing. And, while I don’t know Benioff, I’ll bet with confidence that he craves this information, because he could use it to make better decisions. That’s what I found by working with Bill George – the former CEO of Medtronic and now a professor at Harvard Business School – on True North. In interview after interview, we found that CEOs wanted a better picture of what their employees and customers wanted. CEOs repeatedly told us how unexpectedly isolating they found the job. But when I asked my friend whether he would email Benioff, he demurred, not wanting to ruffle any feathers in the hierarchy.

I don’t understand my friend’s reluctance. The whole way I accidentally became an author in the first place was by sending a cold email to Bill after he spoke with our business school, and briefly shook his hand afterward. I also cold emailed G.E.’s dynamo Chief Marketing Officer and senior vice president Beth Comstock after my last book, Little Bets, came out, and she got right back to me with a mailing address to send it to. Eventually, she invited me to sit on a small Innovation Advisory board for G.E. Beth is a force of nature, and has become a friend. It all started with a guess at her email address based on other G.E. email addresses. And although I’ve never spoken with Jeff Bezos, I have emailed him twice — it’s a poorly kept secret in publishing that if you are an author and have a real problem with Amazon, that’s the “nuclear option.” In my experience, your problem will soon be addressed.

I may be an outlier, but I’m not alone. Blair Taylor is now chief community officer at Starbucks after a cold email the former head of the Los Angeles Urban League sent to CEO Howard Schultz. It led to a phone conversation and ultimately, a job offer.

And Craig Good, a Pixar employee for decades who started at the company as a security guard and left as a legendary employee and member of the technical team, recalls what happened when he sent Steve Jobs an unsolicited email. When Good was working at Lucasfilm Ltd., Pixar’s predecessor, he was in an in-house security and janitorial team, which he thought worked much better than external guard services (where he had also had previous experiences). So as Pixar was building their new headquarters in Emeryville, “I emailed Steve laying out my case that security should be in-house, as in ‘us,’ not contracted as in ‘them’. I Cc’d Tom Carlisle, who was in charge of the project. Steve’s reply was simply, ‘I agree 100%.’ A week or so later I saw Tom in the lunch room and asked what happens next. He said, ‘My experience is that when Steve gives an answer like that no further discussion is necessary.’ Pixar Safety & Security became an in-house operation before the company moved to Emeryville.”

Of course, not every cold email is so wildly successful. I’ve emailed Mark Zuckerberg, Larry Page, and yes, Marc Benioff, and didn’t hear back. I guessed at their email addresses, so maybe I got them wrong. Or maybe they just had nothing to say in reply. Oh well. No skin off my back. It was worth the try.

I learned about the benefits (and associated failures) of cold emailing when I worked as an Associate for Summit Partners, the venture capital firm. Each day we typically cold called or cold emailed dozens of CEOs, since Summit got access to growth equity deals by contacting people directly. I learned a few rules of thumb that I still use today:

Expect a 50-90% failure rate the first time you cold-email someone – i.e., no response. If you don’t get a reply, don’t worry – it’s hardly as bad as calling someone cold and having them hang up on you.

It’s not hard to guess or find an email address. Email addresses are usually firstname.lastname@company.com or, if it’s an entrepreneur, firstname@company.com. You can always call the main phone number and say you’re trying to email something to the CEO, and they will usually give the address.

You are politely persistent if you email once every two days, but probably should give up after 3 or 4 tries if there’s been no reply.

For busy execs, the weekends are by far the best time to try to get a note to them since they typically have more time to read something on a computer screen, rather than a device. And a surprising number of executives do read all their email – especially the personal notes. (Schultz famously does, and imagine how many messages he must receive.)

Keep your message short and to the point. Brevity increases the chances it will actually get read – and relevance increases the chances of a reply.

Does this sound awkward or icky to you? Ask yourself why. You have a great deal of insight and wisdom that the senior leaders of the world would really like to know. A concise email to the right person can open up new possibilities for learning and growth – for both of you.

Too many people are afraid to write. Do it some time and see what happens. Just ask: What’s the worst thing that can happen? And: What’s the best thing?